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Hamptons.com
May 29, 2013

Orient Point: George Washington, Benedict Arnold, And The British Fleet In The Hamptons

T.J. Clementeby T.J. Clemente
in Entertainment
Home Entertainment

Sailing the east end waters one can’t help but think about all the history. Most of it precedes the 1900’s. Starting off, Orient Point, which is the most north point of the North Fork (that other Fork for you Hamptons’ newbies) was a landing place for Indians commuting between Connecticut and Long Island.

The Indians that dwelled on that outer-most section of the North Fork were called the Poquatuck. It was with this tribe that deals were made to buy many of the hamlets of the Town of Southold, mostly back in the mid 1600’s. Then Orient was actually called Oysterponds because of the large shellfish ponds that are still there to this day. Five now-famous families received land grants from the British throne. The names King, Terry, Vail, Latham, and Tuthill are still everywhere. Of course they also had to deal with the Poquatucks.

The Town of Marion was founded in 1836, to honor local native General Francis Marion, who fought with notation during the American Revolution. During the American Revolution the British Navy sailed some of the evacuated British troops from Boston to the South Fork mostly in Sag Harbor and East Hampton Village. Sag Harbor was already a busy whaling port by then. Many of the homes that housed British troops still exist in Sag Harbor. During the Revolutionary War the British supply and support vessels were parked right off Orient point.

Fort Tyler is now referred to by sailors as the “ruins.” (Photo: Capt. Dave Brennan)


The British used Orient as a staging area to launch attacks on many Connecticut coastal towns knowing many patriots from Long Island were hiding there. One of the first official battles of the American Revolution pitched a raiding party sent by General George Washington to where the Plum Island lighthouse now stands to intercept British cattle raiding parties; of course the colonial troops were routed and fled via Orient Point.

In fact, after Benedict Arnold escaped the West Point fiasco and a traitor’s hanging, he served as a British general operating out of Oysterponds (Orient). The Village Lane Tavern in Orient, the home of the founding Vail family, served as Benedict Arnold’s headquarters during the revolution.

Because of the notoriety of the Long Island Town of Oyster Bay during the Theodore Roosevelt Presidency, the residents of Oysterponds decided to change the town name to Orient, associating itself with the notoriety of Orient Point. Twenty-six years before the revolution Benjamin Franklin himself on a commission from the British governor of New York, who in the 1750’s was sometimes stationed in Riverhead, laid down stone “Postal Markers” from Riverhead to Orient Point. Many still stand today. There is no doubt Benjamin Franklin marveled at the view from Orient Point.

The first U.S. Federal Government, with George Washington as President was located downtown in New York City in Federal Hall for one year. That year, Thomas Jefferson and James Madison reportedly shared a coach that stopped in Mattituck at the Historic Mattituck Tavern on their way to view Orient Point. There are reports that George Washington himself visited Mattituck and stayed at the inn, back in 1751.

During the war of 1812 the British War Fleet returned to blockade the Long Island Sound and Gardiner’s Bay. However when they tried to come ashore at Sag Harbor, they were repelled on the docks by men led by a local American officer named Captain David P. Vail. However it was a menacing sight to see the mighty British War frigates off the Hampton’s shores as they lobbed cannon shells into Sag Harbor. Although Sag Harbor was shelled there are no reports of Orient being shelled. It may have been the shelling of Sag Harbor that led to the construction of Fort Tyler in 1898 at the western tip of Gardiner’s Island a point separating Gardiner’s Bay from Block Island Sound. The old fort is now referred to by sailors as the “ruins.” Closed after World War I in 1921, the fort became a target for live practice bombing runs during World War II. Live ordinance is reportedly still there, or so a “danger” sign warns.

The Plum Island Lighthouse stands on land purchased by the United States government from Richard Jerome for $90 in 1826. The rough stoned lighthouse was completed in 1827. When I sail around the Plum Gut I love to look at it.

My boat goes in the water this week, hope to see you out on the Gardiner’s Bay!

Purchased in 1826 for a mere $90, Plum Island (shown here) is a focal point for anyone on the ferry or boaters in Plum Gut. (Photo: T.J. Clemente)

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Calm Before the Storm Fundraising Cocktail Party & Art Show

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Hamptons Hotspot Pink Elephant Is Back

  • Who’s excited for the Palm Tree Music Festival! ⁠
⁠
Check out the Top Hamptons Events This Weekend!⁠
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🎶 5th Annual Palm Tree Music Festival⁠
📅 Saturday, June 21st | 🕑 2pm – 11pm⁠
📍 Shinnecock Indian Territory, Southampton⁠
🌴 Iconic music + luxury vibes + brand activations.⁠
📸: Rob Rich/SocietyAllure.com ©2025⁠
⁠
🛍️ Female Founders Market at The HUB⁠
📅 Saturday, June 21st | 🕘 9am – 6pm⁠
📍 2183 Montauk Hwy, Bridgehampton⁠
✨ Shop curated female-founded Hamptons brands.⁠
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👡 Dolce Vita Pop-Up in Southampton⁠
📅 June 20–22 | 🕚 11am – 3pm daily⁠
📍 95 Main Street, Southampton⁠
🎨 Art, summer style, and new drops each month!⁠
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👜 Kulson Pop-Up at Sage & Madison⁠
📅 Friday, June 20th | 🕒 3pm – 6pm⁠
📍 31 Madison Street, Sag Harbor⁠
🥂 Sip + shop Kulson’s Summer Capsule Collection.⁠
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🍦 BuddhaBerry x Stocked Pop-Up⁠
📅 Friday, June 20th | 🕛 12pm – 5pm⁠
📍 125 Main St, Sag Harbor⁠
🍪 Salted cookie + froyo collab = YUM.⁠
⁠
👜 Hamptons Handbag Festival⁠
📅 Sunday, June 22nd | 🕙 10am – 5pm⁠
📍 15 Montauk Hwy, East Hampton⁠
👜 From vintage to designer. All price points.⁠
⁠
📚 Author Talk: Nellie Sciutto⁠
📅 Saturday, June 21st | 🕕 6pm – 7:30pm⁠
📍 East Hampton Library⁠
🎬 Hear Hollywood tales + get your book signed!⁠
⁠
🎭 Colin Quinn at WHBPAC⁠
📅 Friday, June 20th | 🕗 8pm⁠
📍 76 Main St, Westhampton Beach⁠
😂 Big laughs with the comedy legend.⁠
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🎶 Ghost-Note at Talkhouse⁠
📅 Saturday, June 21st | 🕗 8pm⁠
📍 Stephen Talkhouse, Amagansett⁠
🔥 Don’t miss this epic jam session.⁠
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🥾 Penny Pond Hike⁠
📅 Sunday, June 22nd | 🕤 9:30am – 11:30am⁠
📍 Meet at Red Creek Rd, Hampton Bays⁠
🌲 A beautiful trail to start your Sunday.⁠
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Check out more events at Hamptons.com (Link in Bio)⁠
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#palmtreemusicfestival #hamptons #colinquinn #hub #dolcevita #weekend
  • Hosted in the Hamptons at Calissa, Ja Rule showed off his mixology skills, livin’ it up and serving craft cocktails from Amber & Opal as the premium whiskey brand launched in the Hamptons. 

@jarule 
@calissahamptons 
@amberopalspirits 

#jarule #whiskey #hamptons #calissa #hamptonsweekend #hamptonsevents
  • 24 Saddle Lane, East Hampton, NY 11937⁠
Saunders Exclusive: $2,795,000⁠
⁠
@hamptonsrealestate ⁠
@jenniferwilsonhamptons⁠
@edbruehl⁠
@edmondzenuni_⁠
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This stunning contemporary home redefines modern living with its clean lines, dramatic vaulted ceilings, and walls of glass that flood the interior with natural light. ⁠
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Fully renovated in 2016, the open-concept living area seamlessly blends indoor and outdoor spaces, creating an entertainer’s paradise.⁠
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#hamptonsrealestate #easthampton #hamptons #realestate⁠
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📍 Calissa, Water Mill
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📸 Phillip Faraone/Getty Images for AVA Resort
#calissahamptons #jarule #amberandopal

🍷 Mavericks Montauk Winemaker Dinner
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📸 Photo Credit: Michelle McSwain
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🏃 Beacon of Hope 5K Run/Walk
🗓️ Saturday, June 14 | 9AM
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Support awareness and hope on this scenic 5K through Camp Hero.
#beaconofhope5k #montauklighthouse

📚 Book Signing with Julianne Moore & Jesse Eisenberg
🗓️ Saturday, June 14 | 3–4PM
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#julianneMoore #jesseeisenberg #southamptonny

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Check out more events at Hamptons.com (Link in Bio)

#hamptonsweekend
  • Sydney Sadick, Founder, Editor-in-Chief, and Publisher of Spotlight Magazine has been a lifetime Hamptons goer who has created a platform centered around the community she knows and loves. Spotlight Magazine has strong roots with the East End and is a fresh product in an ever-changing landscape.⁠
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Read the full interview at Hamptons.com (Link in Bio)⁠
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#sydneysadick #hamptons
  • At 55 Long Lane, East Hampton, Share the Harvest Farm is more than just rows of vibrant vegetables and rich soil, but a deeply rooted reflection of compassion and the strength of community. Founded in 2010 by John Malafronte, Ira Bezoza and Peter Garnham, this nonprofit farm was built on a simple but powerful idea, that everyone deserves access to wholesome,  locally grown food.⁠
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For over 15 years, Share the Harvest has partnered with numerous other non-profit organizations to serve members of their community who may be dealing with food insecurity. In a region often associated with luxury and wealth, the farm sheds light on a quieter truth in which many local residents struggle to put healthy food on the table. At its core, Share the Harvest Farm is a place of purpose where every tomato, carrot, and pepper represents the spirit of neighbors helping neighbors.⁠
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Meredith Arm, the Executive Director, and Matthew Quirk, the Farm Director, shared more about the farm’s mission, the challenges they face, and the deep sense of purpose that drives their work each day.⁠
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